Heterocyclic derivatives of hormones have attracted great interest as a privileged scaffold for drug discovery due to their outstanding biological activity. A number of them are potent anticancer agents, which are used in the chemotherapy of breast and prostate cancers. Here, the data obtained by the authors in the field of studying functionalized thiohydrazides as simple “versatile agents” for the installation of heterocyclic moiety to the steroid core are summarized. Namely, a flexible synthetic approach to unknown pyrazole, 1,3,4-thiadiazole, thiadiazine, and pyridazine derivatives of steroids with selective control of heterocyclization patterns are discussed. The anticancer activity of synthesized compounds against breast and prostate cancer cell lines, along with lead-compounds in-depth characterization are included.